Hydrochloric Acid → 2,5-Dimethylquinazolin-4-amine
Reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:3]=1[C:4]#[N:5].[C:11](#[N:13])[CH3:12].Cl>O1CCOCC1>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:10])[N:1]=[C:11]([CH3:12])[N:13]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
1. 66.2 g of 2-amino-6-methylbenzonitrile and 22 g of acetonitrile are dissolved in 750 ml of absolute dioxan and the solution is cooled to 5° C. Subsequently, a weak stream of dry hydrogen chloride is introduced for 8 h. at 5° to 7° C. The mixture is stirred at room temperature for a further 15 h. and then again cooled to 5° C. A further 11 g of acetonitrile are added thereto, hydrochloric acid gas is introduced for 8 h. and the mixture is stirred at room temperature for a further 15 h. The suspension is subsequently evaporated at 30° C. in a vacuum. The crystalline residue is triturated with 0.71 of water, cooled to 0° to 5° C. neutralized with saturated sodium hydrogen carbonate solution and filtered. The crystals are washed with water and dried in a vacuum. There are obtained 107 g of crude 4-amino-2,5-dimethylquinazoline which still contains inorganic salts. This compound melts at 198°-199° C. after recrystallization from ethanol.
Workup
- temperatureagain cooled to 5° C
- stirringthe mixture is stirred at room temperature for a further 15 h
- customThe suspension is subsequently evaporated at 30° C. in a vacuum
- customThe crystalline residue is triturated with 0.71 of water
- temperaturecooled to 0° to 5° C.
- filtrationfiltered
- washThe crystals are washed with water
- customdried in a vacuum
Sources & evidence
- ORD record
- ord-26217f2f2638423ea31b7569fc373d3a
- Source dataset
- uspto-grants-1995_02
- Patent number
- US05387585
Reaction notes
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